While this is perhaps not the ideal time of year to make a trip to Shelter Island, it was a surprisingly lovely last-minute getaway in the winter. I hate sitting in traffic, so I'm a bit reluctant to head out to Long Island in the summer, but after this weekend's trip to Shelter Island, I am going to have to brave it and head back in the warmer months when things are in full swing.
We woke up on Sunday morning thinking maybe we should head out of town for the night given that it's MLK weekend. We grabbed our friend Scott C. (if you don't have his amazing book, Hug Machine buy it immediately!) and hit the road! I checked out hoteltonight.com (first time using this site, but it won't be the last! I love deals!) and I found a good deal for a charming old hotel on Shelter Island.
QUICK TIP – Sites like hoteltonight.com or hotels.com are great places to find last-minute deals, especially if you're going somewhere in the off season! Often we'll even find a place to stay in the car on our way there!
At first it seemed too far to go, but it's actually quite easy to get to! To get there, you drive (or take the LIRR) to Greenport and it's a super quick ferry ride to the island, with the ferries running regularly (even in the winter)! Easy peasy!
We stayed at The Chequit, which is very close to the drop-off point of the North Ferry (certainly walkable if you decided to take the LIRR to Greenport). This hotel has been beautifully updated. The rooms created a sense of serenity, in calming pinks and greys. The furniture was hip and minimal, and I particularly liked the lighting fixtures! Downstairs they've created a cozy hangout zone complete with a fireplace, blankets, board games, etc. A perfect place for a cocktail and to unwind. In the morning we were surprised to see a delicious breakfast spread! We didn't even realize breakfast was included in the stay, so we happily ate up the eggs, blueberry pancakes, and the chia seed pudding (I am no foodie, so I had no idea what this was, but was Alan really taken by it).
Much of the island is closed up for the season, but there are still a few restaurants open. It was 20 degrees out, so after a short walk around we decided we would be more comfortable taking a driving tour of the island. It's small enough that you can allow yourself to get lost and you don't actually end up too far away. My favorite part of the drive was to Ram Head Island. The sun was setting on the drive so we had beautiful quiet views of the water. Everything felt still and frozen. There weren't a ton of options for dinner on the island (sad that the beautiful pub in our restaurant was closed for dinner), but we decided to go to Isola, which was a short walk from the hotel. We loved it! There was a nice bar in the back and plenty of seating in the front. Our chicken parm was wonderful and the service was friendly. The next morning, Stars Café was open to grab some coffee. They also offer a full menu, which we didn't have a chance to check out, but seems like a perfect place to grab some sandwiches in the summer and head out for the day. That was it! It was a very short trip, but incredibly relaxing. I can't wait to check out Shelter Island in the warmer months!
On our way back we poked around Greenport, Long Island. I really like this town! Some of the town was closed, not sure if it was the season or if it was due to MLK Day. Either way, there were enough stores to pop into that it was fine. I have been out here before and in the summer it's quite bustling.
I really like a vintage shop there that is clearly very thoughtfully put together, The Times Vintage. I happened to be in Greenport in 2013 when it had just opened and was talking to the proud dad of the girl who opened the shop. It was sweet, as are all of the goods in there. They've got everything from 1950s cocktail dresses to mid-century furniture, kitchenware, and other furnishings.
The town also has plenty of other shops that are thoughtfully curated where you can buy candles, beautiful cheese plates, and jewelry. We ate at a place called Andy's that is very family friendly. In the front of the restaurant are games for kids to play with and an area for them to cruise around. But my most favorite part is that you get FREE POPCORN when you sit down! I smelled the old-timey popcorn machine immediately, so I was sold right then and there.
Finally, for kids, there is a carousel in town that operates year-round as well as a cute little ice skating rink right next to it. Greenport is cute all the time, but definitely a place to go back to when it's in full swing!
On our drive out to Greenport we noticed signs for the Long Island Aquarium in Riverhead, NY. Given how cold it was over the weekend, we thought it would be a great indoor stop on our drive back to Brooklyn. Boy were we right! This place is GREAT! The entire place has "Lost City of Atlantis" vibes with ancient ruins (you can see a statue of Poseidon's arm holding his trident in the shark tank). They have a butterfly exhibit where you walk around a small garden with butterflies flittering around you. Then, if you dare, you can go into the bird room where you can buy some bird seed for $1. These birds are very friendly and will land on your shoulder, head, arm, etc. Terrifying to people like me, but lots of folks seemed to enjoy the experience. Speaking of experiences, there are LOTS of different experiences you can have at the aquarium (for a price). You can swim with sharks (you are in a cage), go snorkeling, and even meet a penguin. The aquarium wasn't very crowded, but I'm curious what it's like on a weekend when the weather is nice. It is not terribly big, so it could possibly be less pleasant when crowded? I guess we'll find out next time we head there! Overall, an enjoyable afternoon that I'd definitely recommend!